The One that Got Away
by literallyliterati
Summary: After the revival, Jess becomes an important part of Rory and her child's life. This is the one shot version where they don't end up together.


**A/N: If you're reading Aftermath, it will be updated and eventually finished. It turns out making the idea longer than planned and fitting with what I want to happen has been harder than I thought it would be. I've also been really busy on top of other things but hope to update soon.**

 **This is a different story. I've had this in my head for the majority of this past year. I've been writing to write this for months and even made a video towards the beginning of the year to fit the story this will tell. When my copy of A year in the life DVD came in the mail and I rewatched the revival again, it, for lack of a better word, revived this idea and my inspiration to write a post AYITL fic. It's just been taking me a while to finish it now.**

 **There will (hopefully) be two. This will be the shorter of the two and also I've gotta warn my readers - this isn't a Literati ending. Ever since the revival premiered, I began to reevaluate my otp. For years, I believed if there was more gilmore girls, it'd have to be Rory and Jess endgame, there wasn't any other choice and they were meant to be.**

 **But then after seeing that she'd rather date Paul who she couldn't remember and begin an affair with a man she didn't want to marry instead of ever giving Jess a second chance, I changed my mind. Then I started thinking about when they were together and while the good stuff was shown offscreen and did happen, they were doomed from the start because of how Rory regarded him. Season three Literati was a mess and I believe Jess needs to move on once and for all.**

 **If you aren't interested in that, even though this will be short, I figured there should be something ahead telling what it is.**

 **Also, it bounces around a lot. It only goes forward but I feel it should be a warning ahead of time. I hope it's not hard to follow.**

 **Now onto the story.**

Rory took a deep breath and counted to ten. The cool tiled floor of the bathroom beneath her felt hard as a rock. Kirk had been right. The downstairs bathroom was bad on your knees. She leaned her head against the wall and closed her eyes.

"They really need to rename it from morning sickness," she mumbled to herself in a whisper.

It had been two weeks since her mother had married Luke. In that time, she'd taken up residence in Lorelai's house, the house she'd grown up in. It was almost comforting to be able to stay here while her life had fallen apart. Just as she was finding her way back, she'd gotten a phone call from her doctor about results from a test she'd taken. That was when it all changed.

Tomorrow, her mother and finally official stepfather would return from their honeymoon. Rory didn't want to be a burden to the newlyweds, no matter how much her mother had insisted she wouldn't be. She really needed to find a place to stay. Right now, though, she felt perfectly fine seated on the bathroom floor as she awaited more of her morning sickness.

Then she faintly heard knocking. She gripped her heads tight to the floor, almost stuck. Who would be at the door? Before her thoughts could run through a list, starting with Lorelai returning early, she heard the door open and her question was answered.

"Hello?" Jess asked as he came inside the house. "Rory? Are you here?"

Her eyes widened as she scrambled to get herself off of the floor. She quickly flushed the toilet and washed her hands and face. Within seconds, she opened the bathroom door and was met face to face with Jess Mariano. "Hi. I'm here."

"Hi," he said, surprised to see her even though he thought she might be home.

"What are you doing here?" She asked in an easy tone as she made her way out of the bathroom doorway and out into the living room. "I thought you were coming tomorrow when you pick up mom and Luke."

"I got bored," he shrugged. "Running a publishing company sometimes gives you much freedom."

She sat down on the couch and it didn't slip her mind how Jess didn't sit at all yet. "No new books to edit or release?"

"Not yet," he smirked. "That is, until Gilmore Girls is ready."

Rory shook her head. "It's only a few chapters. I don't even know if it's any good."

Jess gave her a strange look. "You have ten chapters."

"Eleven," she corrected. "I finished another one yesterday and was gonna tell you tomorrow when you came."

"See?" He smiled. "It'll be our next book in no time."

"Are you serious?" She asked. "You'll publish my book?"

"If you don't want me to or if you get other offers -" he began.

Rory laughed. "I don't think I'll be getting many offers, first of all."

Jess didn't comment. She took his silence to mean he agreed with her even though the look on his face said otherwise.

"Besides, would it be weird?" She asked. "Your company publishing my book?"

"Why would it be weird?" Jess finally sat down and on the table directly in front of the couch.

"Because we dated?" She tried to frame it as something funny. Whenever she thought about their past, funny was the last word she'd use to describe it.

"Was that you?" He teased and she grabbed the nearest pillow and hit him on the arm. "Rory, it's only weird if we make it weird. Do you want it be weird?"

"No," she answered honestly. "It's just - you're gonna be in there. You know that, right? Would that give some kind of bias?"

He shook his head. "No. Not unless you painted me any different than I was. And to be honest, I was an ass back then so I wouldn't blame you for how you portray me."

"You were no more one than I was," she replied with a small smile of her own.

"Please," he scoffed. "You're a lot of things, Rory Gilmore, but that is not one of them."

"You don't know some of the stuff I've done, Jess," she told him. "There's a lot I wish I hadn't."

"Like what?" He wondered. He seemed genuinely curious.

"Things," Rory shook her head, regretting saying anything. She didn't want to open up about her past or even her present situation.

Instead she changed the subject to her hunger she had gained since feeling sick moments before. Jess went along with it as she grabbed a jacket and they headed out the door, thankful she had brushed her teeth before leaning on the bathroom floor.

…

It's only a week later when Rory finds out about Logan. She had gone to Philadelphia for the weekend, against her mother's objections to give Jess the latest chapters. In the short seven days, she had written out two more chapters. The growing pregnancy had made her even more determined to finish before the baby made its way to the world.

When she arrived, everything was normal. Instead of going to Truncheon first, she went to Jess' apartment. She had only been here a couple of times before but the address burned into her memory. It was just so Jess.

It still amazed her how perfect he fit into his life and how much he had grown up. Rory was proud of him, the way you'd be proud of anyone important to you or that you saw potential in them when no one else did.

When she arrived at his apartment that day, his newspaper was still outside the door. Rory picked it up, not thinking much about it and knocked on the door. Jess opened it, a smile on his face at the sight of her.

"Hey," he said.

She smiled back. "Hey."

"Was I expecting you?" He asked, hoping he didn't forget they had plans.

Rory shook her head. "No. This is completely spontaneous and selfish."

"Selfish how?" His eyebrow rose as he let her inside then shut the door.

"I wrote more chapters," she beamed. "My mom doesn't get it. I mean, she does but she doesn't. Does that make sense? I was thinking 'who would appreciate this feeling of books and writing like I do?' I got in my car as soon as I thought of you."

"Don't I feel honored," he smirked. "You want something to drink? Coffee?"

She hesitated. If she said no, he'd know something was off but if she said yes…

"Rory?" He called out. "You okay?"

"Yeah, sorry," she laughed it off. "No coffee. This will be quick. Can I just have a water?"

There was questions written on Jess' face but he didn't comment. "Water it is."

She sighed in relief, thankful he didn't ask questions. "Hey, is it okay if I read your newspaper?"

"Go nuts," he said from the kitchen.

Rory grinned happily, excited to feel the pages in her hands. The front was some story about the disastrous election. She flipped through the pages for something to read when she saw it.

Hidden around other society news was a picture of Logan and Odette. The announcement stated how their wedding was this weekend. Rory wasn't sure when exactly she had started to cry. At some point, she felt wetness on her cheeks and touched her face only to find drops.

When Jess entered the room again, he instantly noticed. He rushed to her side on the couch. "Rory. What's wrong?"

She showed the newspaper at him. "He's getting married."

Jess looked at the picture and the words in his hands. "Blonde dick. Wow. I haven't thought about him in a long time."

Rory laughed through her tears. "It'd be a little weird if you had."

"But why are you?" He wondered. "You guys broke up a long time ago, right?"

"We did," she agreed but knew she couldn't not tell him. "But recently...we started something again. While he was engaged."

"Oh," he said. "I didn't - I didn't expect that answer."

She laughed again but this time humorlessly. "It was stupid. I don't know what I was thinking. I had a boyfriend of my own, too."

"Why then?" Jess wondered. "Sorry. It's none of my business."

"It started right after -" she sucked in a breath while Jess patiently waited. "After my Grandpa died. Logan called me to see how I was doing and then we ended up bumping into each other."

"And that's when it started?" He questioned, unsure how he was able to be so calm talking about her sleeping with Logan while both of them were in relationships.

"Not right away," she shook her head. "He offered to come back to Connecticut with me for the funeral. I told him stay behind. When I went back to London afterwards, he was waiting for me at the airport. That's when it started."

Jess took a deep breath. "You were in a bad place. You just lost your grandfather. You can't be blamed for that. Grief doesn't really have logic."

"Yeah but that may work for the first few times," she scoffed while she wiped away tears. "But a year? I don't think grief gives you a permit for carrying on an affair for a year."

"A year," he repeated. "So that means you two -"

"We were broken up when you came this summer," she replied. "I broke it off."

"That was months ago," Jess pointed out.

"Yeah but something else happened," she sighed, preparing to come clean. "Logan came to Stars Hollow about a month after I ended things. He brought our old friends. We ended up buying out an entire inn. I should've stayed in my own room. I should have left."

"What -" he stopped and began again, processing how she just told him about her staying in Logan's room in an empty inn. "What happened after that?"

"I ended it again," Rory sniffed. "but the kicker is Logan told me he was still marrying her no matter what. He offered me somewhere to stay, like he was hiding his mistress. It was then that I realized not only did Logan not love me but I didn't love him."

Jess sighed in relief. "So then why are you upset? If you didn't love him and he's getting married -"

"Something else happened that night at the inn," she sniffed again. "I didn't know back then. I felt sick after and then I was late so I went to see a doctor."

"Oh," he said to no one but himself.

"Jess, I'm pregnant," she didn't look at his face as the words came out. She was afraid to see the judgement or the reaction she was sure would come. "I'm pregnant and the baby's father just getting married in a week."

Her sobs came out harder this time. Jess moved himself closer to her and wrapped an arm around Rory. "Hey. Ssh. It's gonna be okay."

"How?" She gasped between sobs. "I don't know how to do this! And Logan! What about him? I still haven't told him and I'm not sure if I even should."

"You'll decide what's best for you and the baby," be told her. "Don't worry about Logan yet. Think about you and the baby."

Rory nodded into his chest, soaking his jacket that be still hadn't removed. "I'm scared, Jess."

"You don't have to be scared," he rubbed her arm. "You have your mom, Luke, Lane, all of that crazy town...and you have me."

Rory moved herself out of his arms to look at his face. Whatever she was looking for must not have been there. "Really?"

"Yeah," he agreed. "I'll always be here."

…..

Lorelai slowly sees it. Jess had been visiting Stars Hollow more again and when he had, a lot of time was spent at Rory's new apartment. He set up the crib, painted the walls. He even went to one of the doctor's appointments with Rory. It was as if he was the father and not Logan.

And that was why she had to ask the questions burning on her mind.

"Jess has been here a lot lately," Lorelai said to her daughter one afternoon.

"He's been helping out," she said. Her seven month pregnancy bump stuck out as she sat on the couch across from her mother.

"A lot though, right?" She pushed.

"Yeah, I guess," she agreed. "He's been a good friend, especially since I told him."

"And that's all he is?" The older woman wondered. "A friend?"

"Of course," she answered. "Why? Did you seriously think there was something going on? Have you seen the bump?"

"Some people don't go away because of the bump," she suggested.

"We're just friends," she defended.

"Okay," she nodded. "if you say you're just friends, then I believe you."

The final weeks of Rory's pregnancy passed. Lorelai's words rang in Rory's head constantly afterwards, haunting her. Was she and Jess just friends? He had been spending a lot of time with her. The next time he'd come over after that conversation, she was so distracted that she couldn't even hold a conversation.

The night Rory's water broke, she was alone. Immediately she grabbed her phone and called her mom. Lorelai wasn't far away and with her came Luke. As she waited for her mom, she called Jess out of habit. He was in Philadelphia for the weekend but she couldn't help it. He didn't answer so she hung up and waited.

….

At the hospital, a full day after arriving, Victoria Leigh Gilmore was born. Rory's head leaned against the pillows in exhaustion. The hours in labor had felt exactly as her mother had described it. She would be sure to remind her daughter of this every year on her birthday just as her own mother had.

Lorelai had been in to visit and so had Luke. Lane and her family stopped by along with Paris. They were still waiting on Emily and it was a pleasant surprise when Michel and Frederick had showed up.

Just as Rory was about to go to sleep, relaxed ever since she held Victoria, named after her and her mother's middle names, there was a knock on her door. Rory sat up instantly and her breath was almost knocked out of her when she saw who the visitor was.

"Hey," Jess said as he walked in and shut the door behind him.

"Hi," she replied in the same tone as his.

"Is this bad timing?" He asked. "I wasn't sure if there was a time restriction of when to visit new mothers."

"No time restriction," she shook her head with a small laugh. "I just didn't expect to see you."

"You called," he pointed out. "I was at work late and my phone died. It wasn't until a few hours ago I saw that you called and I called Lorelai to ask what was going on."

"I'm sorry I didn't leave a message," she sighed. "How do you say 'hey, I know you're in a different state but do you wanna come to the hospital because I'm having another man's baby?"

"You could just say your water broke," he replied with a smile.

"Hey, Jess?"

"Yes, Rory?"

She smiled sweetly. "My water broke."

"I can see that," he teased. "How are you feeling? Tired?"

She shook her head. "Not really. It was everything my mom said and more but I don't know, I feel good. I feel happy. She's here, Jess. My daughter is here."

"Did you keep the planned name?" He asked her.

"Victoria Leigh," she smiled. "My mom is so proud of me for including both of our names in hers."

"And Logan?" he finally brought himself to ask. It didn't escape him how the father wasn't here for their birth of his child.

Rory shook her head. "No."

"He couldn't come or didn't want to?" He wondered.

"He has work," she waved it off. "He lives in London. He can't just get here."

"Yes, he can," Jess argued. "He's rich. He'd find a way."

"It's a good thing you're not my attorney because if you point out he's rich, they might think I'm setting him up," she joked.

"Would he think that?" He asked seriously.

"No but his family might," she fidgeted under his gaze. "It doesn't matter anyway. I didn't call him. I don't expect Logan to fly across the ocean to come."

"Does he even know?" Jess found himself asking.

"He knows I got pregnant," she answered honestly. "Not that she's been born."

Jess sighed, thoughts of his own father came to mind. "Give me your phone."

"What?" She was surprised. "I don't have my phone -"

"Yes, you do," he held his hand out.

Rory reached over to the table besides her and went into the first drawer. She pulled out her iPhone and handed it to Jess. "What are you going to say?"

"I haven't decided yet," he admitted. "But as much as a dick as he may be, he should know his kid's been born. Got to give him that at least and what he does after that is up to him."

Rory nodded, tears forming in her eyes. He gave her a tight smile as he walked out into the hall and down to a part less crowded. Jess scrolled through Rory's contacts. His own name flashed at him as he headed for L.

Once he found Logan's number, he hit dial. It rang a few times before it finally picked up. "Huntzberger."

Jess felt ice as he heard that voice. Memories of a dinner gone wrong flashed back to him and he remembered yelling at Rory outside the bar about Yale. The voice said hello as a question on the other end and it sparked him to speak. "Logan Huntzberger?"

"That's me," a slight chuckle erupted on the other end. As if he found this amusing and this happened often. "May I ask who this is?"

"My name's Jess Mariano," he sighed. "I don't know if you remember me but we met years ago at Rory's grandparents' house."

Something must have clicked in Logan's head as he put it together. "Kerouac. To what do I owe this pleasure?"

"Rory's in the hospital," he said. "She just had a baby, your baby and she was scared to call you. Now I don't particularly like you or even care about you but I grew up without a dad. I thought you should be the one deciding whether or not you want to participate in this kid's life or not."

Logan is silent on the other end for a few seconds. Jess almost considered hanging up before finally he heard a question. "What hospital?"

…

After Logan's appearance at the hospital following Victoria's birth, he came clean to Odette. She honestly wasn't surprised but knew that by now, she was too far into the relationship. She decided to stay with Logan but only if he promised this was the first and last time.

Jess had watched Logan enter the hospital and bravely ask Lorelai where Rory was. Lorelai and Luke had both given him the glare of a thousand scorns but it didn't stop him. If Emily Gilmore had been there and not downstairs in the gift shop, she'd have done the same thing. Logan stopped at Jess, remembering this man he belittled years ago.

"Thank you for calling," he said as Jess just nodded in response. Then he went right in the direction of Rory's room.

Logan was at the hospital for a while it seemed. He talked with Rory and it didn't escape her family how they'd brought little Victoria in so he must have met his daughter. When Emily returned and discovered who was there, she almost called security before Lorelai stopped her. She knew this was something her daughter needed to do and Jess had to admit he agreed.

….

Logan had become a fixture in the Gilmores lives. In the twelve months since Victoria Leigh had been born, he'd visited his daughter frequently. When his own family had found out, they were furious. Logan shrugged them off and left the family company, moving he and Odette back to the States to be closer. It surprised everyone that he and Rory having a child gave him the push to cut off his family once and for all.

As her first birthday approached, Rory struggled with the guest list. She knew she'd invite the people of Stars Hollow but wasn't sure of who outside of that besides Paris and Jess. Paris would bring her own children and she wondered if Logan would come.

Lorelai was the one who pushed her to tell Logan about the party. She listened to her mother and was genuinely surprised when he told her he'd come. He asked quietly if he could bring Odette and if it was too weird, he wouldn't. Odette had already accepted this and she didn't want to separate father and daughter, he explained. Rory found herself telling him his wife could come even though she did in fact think it would awkward.

The party was a success. Little Victoria - now nicknamed Tori, just as her mother's name was shortened - seemed very happy. It didn't take much to please her. Her favorite people outside of her parents were Nanny Lorelai, who refused to be grandma, and Jess. He was still in shock but saw her delight at his visits each time he came.

During the party, Jess had escaped to the upstairs diner apartment. It still looked the same but it didn't. The six months Jess had lived here years ago reflected in its walls. He smirked to himself as he remembered those months and how it was weird Rory hasn't visited in any of them. It all began to make sense as he thought of his ex-girlfriend's life. He was glad her and Lorelai had been doing better since Tori came along.

Logan hadn't brought Odette after all. He realized how weird it might be, Jess figured. Not that inviting your wife to the birthday party of you and your mistress's child would ever not be weird.

And it was exactly Logan that was the reason Jess escaped to the apartment. He wasn't sure how much he could stomach before the sickness took him over. Logan behaved as a doting dad and Rory let him. He needed a break from that even if just for a little bit.

Just as he'd been about to return to the party, he heard the Bell jingle above the diner front door. It's signal to someone's entrance planted Jess in his spot the second he heard who it was down there.

"So what did you want to talk about?" Rory asked.

"I'm not sure how to say it," Logan sighed.

Rory laughed lightly. "Come on, Logan. You've never been someone to hide what you want to say."

Logan let out a small laugh in return and Jess felt his stomach drop. How could they joke and laugh together? He was sure he'd never understand their relationship or Logan's hold on Rory. "It's just me and Odette have been talking…"

"Oh," she seemed surprised. "Odette, huh? She isn't leaving, right? It's my fault that -"

"No, no," Logan cut her off. "Nothing like that. She told me she accepted this part of my life - you and Tori - and she is keeping her word."

Jess opened the apartment door and glanced down the stairs. He saw Rory nod to his words. Her face looked curious and confused. "Then what is it?"

Logan sighed again. "I want joint custody of Tori."

"What?" She was stunned.

"You heard me."

She shook her head twice from side to side. "Yeah, I heard you but I don't quite believe my ears. You want joint custody of Tori?"

"Yes."

"Logan, when you found out about her, we decided she'd stay with me," she stayed as calm as possible but her face looked angry. "You said you didn't want to make it weirder for Odette so you agreed."

"That was then," he shoved his hands into his pockets.

Rory stepped back. "What changed? You were fine with this arrangement. You come and visit her whenever you can and she stays with me. Logan, that was the deal. We didn't even fight over it but now you're telling me you want to take her away from me?"

"Not take her away," Logan defended. "I want to be able to know when I'm getting time with her. I want her to come stay at my house and to have her own room there. I want her to know her father as not just someone who comes to her mother's house for a quick day visit. I want her to stay over and I want Odette to be her stepmother for real."

"Uh-huh," she nodded as she tried to process what he said. "How did Odette get you to agree to it? Did she say how Tori's your daughter too and convince you that she's better off with you than me?"

"That's not what she did at all," he replied. "She simply expressed to me that I deserve to raise my child, too. And she's right."

"So I'm just supposed to hand her over?" Rory questioned.

"No -"

"Logan, you told me you didn't want to raise her," she recalled.

"Everyone has the right to change their mind," he pointed out.

"They do," she agreed. "But not everyone is talking about my daughter. You wanted to be the fun dad who drops in. You didn't want this. How do I know if we do this, joint custody, that you won't change your mind again?"

"Rory, this is my daughter," Logan said.

She scoffed. "I'm aware. I was there the night she was conceived in New Hampshire."

"Rory."

"What?" She turned on him angrily. "You think just because you ask, I'll be okay with this? Logan, you didn't even want her at first. It took a long time for you to adjust. That's why I didn't tell you when I went into labor. Tori needs someone consistent in her life."

"I will be consistent," he pleased.

"I need to think about it," she told him.

"What's there to think about?" Logan argued. "I'm her father, Rory. I deserve to see her not just in your home."

"I can't do this right now," she sighed.

"Rory."

"Please go, Logan," Rory said. "I'm not saying you have to leave the party but I really need a moment right now before I go back out there and I'd like to do it alone."

"All right," he agreed and started to walk away. "I guess I'll see you around then."

With that, he was gone. Rory sniffled as she let tears fall. Jess watched sadly before going back up into the apartment.

….

The day Jess found out that Rory had granted Logan joint custody, he headed to see Matt and Chris. It's been a while and he decided he needed something to take his mind off of what was going on in Stars Hollow.

They took him out to a bar where it was open mic night. Jess reluctantly went into the bar, reluctantly drank what his friends put in front of him and listened to whoever went on the stage.

They had been there for an hour already. After a bunch of drunken performances, a girl went on stage. She wore a hat and had her long brown hair down. Jess couldn't see her face yet as she had it down towards the ground, turned to the mike. And that's when she began.

The girl on stage began to sing. A slow song he didn't recognize floated through the air and finally, she lifted her head. Jess almost felt his heart drop. She was beautiful. The most beautiful girl he'd seen, only after the other brunette he'd never been able to fully get over.

His friends noticed his expression and theirs seemed to show pride. They were happy they brought him here tonight.

After she left the stage - just two songs later - Jess was out of his seat. The girl went to the bar to order a drink, clearly her nerves were active after her performance. He almost didn't make it to her but then decided "what the hell?" And approached her anyway.

"That was a really good set," he said as he came up to the stool next to her.

The girl turned, her face gave no sign to if she was okay with this move or not. "It was only two songs."

"But a good two songs," he corrected which earned a small smile. "You were great up there."

"I was a little nervous," she shrugged as the bartender placed her drink in front of her.

Jess eyed it with a smirk. "Clearly."

She laughed and ducked her head. "That obvious?"

"Nah," he shook his head. "I only noticed because I was paying attention to you."

"Oh?" She raised her left eyebrow. "And does this line - does it usually work?"

Jess laughed. "No. But I gotta be honest, I've never tried to talk to someone who performed on open mic night so maybe it would."

"Oh," she extended the word. "And how you do think it's going now?"

"I think you're still talking to me," he answered. "Which means you're either interested or just really curious to see me crash and burn."

She took a sip of her drink but didn't answer. Jess watched her, waiting. She had bracelets around her wrist, filled with colors. Her hair was a lighter brown than it had looked on the stage, too.

When she didn't answer, he continued. "I guess what I wanna ask is...how am I doing?"

"You're doing good," she nodded with a smile.

"Good enough to know the name of who I'm talking to?" He asked.

She laughed. "Rebecca. My name is Rebecca."

"Hi, Rebecca," he held out his hand to shake. "I'm Jess."

…..

"I'm just gonna tell him when he comes," Rory exclaimed.

"Are you sure?" Lane asked. "You haven't even seen him in months."

"I know," she wringed her fingers together. "But it's been in my head for months. And after the custody stuff - he was there for me."

"Until it happened," Lane pointed out.

"That may be true but I can't expect him to just move his life around for me," Rory replied. "We're not even together and he's been with me through my pregnancy and raising Tori and then getting ready for the hearing. He had to get back to his own life sometime."

"And you're sure this is the right thing to do?" She questioned. "The right way?"

"Yes," she nodded. "No. Lane, I don't know."

"Okay, first of all, stop pacing," she told her from her place on the couch. "Calm down. Take a deep breath. Now tell me what you would tell Jess."

"Isn't this a little weird?" She asked.

"Of course," she rolled her eyes. "But tell me anyway."

Rory tried to answer. She sighed, opened her mouth but closed it. Seconds ticked away and she still came up empty. She sat down and put her head in her hands. "I don't know what to say."

"That's okay," Lane assured her.

Rory lifted her head. "Is it? I mean, I wanna tell him that I have these feelings for him but I don't know how to say it. I don't even know exactly what the feelings are. All I know is that I feel happy when I'm around him. Like genuinely, heart fluttering happy. And it doesn't feel entirely friendly and then I see him with Tori and it feels like we're a family. The three of us, like he's her dad."

Lane smiled at her best friend which made Rory question her. "What?"

Lane shook her head. "That's it."

"What's it?" She asked.

"That!" She pointed at Rory. "Right there. What you just said. That's what you're going to say to Jess."

Rory smiled as she realized maybe she could actually do this.

…..

When everyone arrived for Thanksgiving dinner, just a few days after she and Lane discussed what to say to Jess, Rory felt like she had to mentally prepare herself. At first, she was gonna just ask if they could go to dinner and she'd tell him there. But then it occurred to her that if he didn't feel the same, they'd be obligated to finish a dinner awkwardly.

That plan was scratched. Next was just telling him alone while everyone got ready. That seemed like the best plan in her head. They could avoid awkwardness if he didn't feel the same because there'd be other people there. And if he did, they didn't have to avoid anything. It made sense.

People piled into the inn, just as they had for the bracebridge dinner. Tori was still napping so Rory stayed with her while most people arrived. Lorelai knew of what Rory's plans were, she even did a few variations of "I told you so" when her daughter told her.

But after the initial teasing, Lorelai sat down, held her daughter's hand and told her what a good man Jess had become. Lorelai explained that she supported her and that if Jess was who she wanted to be with, that it was a good choice after not only how he was with Tori but how much he had changed over the years. Rory nodded, eyes filled with tears and hugged her mother.

But now, she was fearful. She told herself that she hid with her daughter because it was nap time. But Rory knew it was more than that. She couldn't face Jess yet. It was scary to tell someone who used to love you and she used to love them that maybe you did in fact love them again. She wasn't sure what his reaction would be and it made her afraid.

When Jess' car pulled up, Lorelai rushed to Rory. She told her how he was there and she might want to get to him before Miss Patty did. Rory asked her to watch Tori, there wasn't long left to her nap anyway, especially since she'd be awake as soon as more people arrive.

Rory headed out to the main room of the Dragonfly and stopped short. Jess was talking to Luke in the doorway already. Her eyes took in the sight of him, in front of her after months away. He looked possibly even better than the last time she'd seen him.

Jess is smiling. He looks happy, she notes. Rory smiled to herself as she watched him. This person he'd became in their time apart the first time was who she always knew he could be. She was proud of him and right now, deathly afraid of telling him how she felt.

She walked closer and as their voices get into her earshot, she hears a word she didn't entirely expect.

It's Luke who says it. "So you brought your girlfriend, right?"

Jess nodded, a beaming smile on his face. "Yeah, yeah. She wanted me go ahead and see everyone first. She'd hiding in the car, actually."

Luke laughed. "First you hid girls in the closet, now it's the car."

"Circle of life," Jess joked.

Rory was about to turn away when they spotted her. Jess called out her name, almost surprised to see her even though it was obvious he would considering. She turned and plastered on a smile. "Hey, Jess."

He moved forward to hug her. It felt awkward at first, not like any of these hugs they had shared in the past two years. If he wasn't suspicious from her trying to leave, he should be by now.

When he pulled out of the hug, he looked at Rory. "What's wrong?"

"Nothing," she shook her head. "I just didn't want to interrupt the two of you."

"You're not interrupting," Luke told her. "Is Tori still down for her nap?"

"Yeah, Mom's with her right now," she answered.

"I think maybe I'll go check on her," he said, an obvious attempt to leave the two of them alone. "I'll meet your girlfriend later then?"

"She'll be here," Jess nodded, a small smile.

Rory turned, an act of surprise on her face. "Girlfriend?"

"Yeah, Rebecca," he confirmed. "I brought her with me. I hope that's okay."

"It's fine," Rory smiled. "I didn't know you were seeing anyone."

"It's still fairly new," he replied. "It's only been a couple of months."

"Oh," now she really was surprised. "And you brought her to Stars Hollow. That's pretty brave."

Jess laughed. "Yeah, I guess it is. But you know, she wanted to come and I don't know, the part of me that would usually run from this - well, he doesn't want to be running away anymore."

"Oh," she said, her voice almost displayed her feelings. "That - that sounds serious."

He nodded. "It is. Or at least I think it is."

Rory was about to ask another question when a pretty, tall brunette came inside and walked right up to Jess. His head turned and she could just see the expression on his face. He was happy.

"You decided to come in," he commented.

The girl who must be Rebecca laughed. "The car was getting cold and I thought maybe you had enough time to tell people to be nice to me so I could come in."

"I don't need to tell people to be nice," he replied. "Once you meet everyone, you'll see the pleasantville side of the town. They're only not nice to hoodlums and bad boys."

Rory watched them curiously, remembering moments ago when she was preparing to tell him about her feelings for him. It seemed like a distant past now as she watched them together.

"Oh!" Jess said. He turned to Rory. "Rory, this is Rebecca, my girlfriend. Rebecca, this is Rory."

"Hi," Rebecca said, a smile on her face. "I've heard so much about you. It's so nice to meet you."

"You, too," Rory said and she couldn't not genuinely smile back. "I've gotta ask though - how much is so much?"

Rebecca laughed. "Not anything bad. He mentioned that you guys dated in high school, that you became friends again years later."

"That's not so bad," Rory said back.

"Oh!" Rebecca exclaimed. "And he mentioned you have a daughter."

"Tori," Jess said. "How is she? I feel like I haven't seen her in a while."

"She's good," Rory nodded. "Should be waking up from her nap soon. She'll be happy to see you."

"Hey, can I ask something?" Rebecca asked. "Where's the restroom? We've been on the road for a little bit and -"

Rory cut her off. "Down that hallway to your left."

"Thanks," Rebecca smiled and headed out but with one last sentence. "It was really nice to meet you."

Jess turned to Rory, curious. "So what do you think?"

"She's really nice," she answered honestly. "And you look happy."

He blushed, something she'd rarely seen him do. "Yeah?"

"Yeah," she agreed.

"Good," he said. "Because I am happy."

"I'm happy you're happy," Rory said to which they both laughed.

Lorelai came up behind them. "Hey, you two, what's going on?"

"I thought Luke went to find you," Jess commented while lorelai moved to hug him.

After he hugged her back and she pulled away, Lorelai shrugged. "He did but now he's watching Tori sleep."

"I just met Jess' girlfriend," Rory stated.

Lorelai raised an eyebrow at her daughter in surprise. "Oh?"

"Yeah," she nodded.

"I didn't know you had a girlfriend," Lorelai accused Jess.

"Just hiding her from the town of Stars hollow until she wanted to come," he said. "Aunt included."

Lorelai gasped in mock shock. "Well! I see who doesn't want a hello Kitty laptop case for Christmas."

"I have never wanted that," he laughed.

"And now you're not getting one either," she huffed.

"On that note, I think I'm gonna go look for Rebecca," Jess told them. "make sure she didn't get lost."

He excused himself then headed into the direction Rebecca had gone into.

"So," lorelai said. "Jess has a girlfriend."

"I guess so," she rocked on her heels.

"Does this mean you're not going to tell him?" She wondered.

"No," Rory shook her head. "No. I'm not telling him."

"Hun."

"He looks happy, mom," she said. "Genuinely happy. Me - I'm a mess. I'm not gonna do anything to put his relationship in jeopardy just so he can deal with me."

"Hun, he doesn't deal with you," she corrected. "If it was just dealing with you, he'd have given up a long time ago."

"I'm not doing it, Mom," she explained. "I've gotten in the middle of relationships before with my stupid feelings. I didn't think with my head but I was selfish with my heart. I've made a lot of mistakes - Dean, Paul, Logan - and I'm not doing it to Jess."

"All right," she nodded. "All right."

…

Months passed and months became a year. Rory had seen less of Jess but also he had visited Stars Hollow frequently. Whenever Rebecca was with him, she tried to not be in the way as she found her feelings didn't weaken. Every time she saw him, the same flutter came back and she wished she had said something to him sooner.

She wished she did a lot of things differently, starting with how she treated him in high school, always comparing him to Dean. She realized she always out others above him, especially Logan and even Paul, weirdly enough. She had dated a man she barely remembered or invested in their relationship instead of giving Jess another chance.

She realized she deserved to see him move on without her. He deserved to be able to do that.

So when the phone call came, she wasn't surprised. Jess, once a small town bad boy who broke her car and her heart, who had only loved her for the longest time - he was getting married.

And she was invited.

…..

The wedding was small. Jess didn't invite many people that he knew. Some faces Rory recognized, some she didn't. Lorelai squeezed her hand as they entered. Luke held Tori in his arms so she wouldn't fidget in her flower girl dress. It seemed fitting that her daughter would be in the wedding even if she wasn't, Rory thought. Jess loved Tori like a daughter as Tori has loved Jess like a father. She'd never take that away from her.

It was a beautiful ceremony. Jess' face when his bride walked in was incomparable. She'd never seen his face light up like that. A test had slipped down her cheek as she watched them recite how they loved each other and said their "I do's".

…..

The next year, there was another surprise visit from Jess. Ever since the wedding, he hadn't been around as much and stayed mostly in Philadelphia. Rory has finally published her book. Even if he wasn't around, Jess had made sure Truncheon had done it for her. Logan also has turned out to be a good father, despite the circumstances. It wasn't surprising he now had a son with Odette.

But this was different. When Jess came, Rebecca wasn't with him and he headed straight for Luke's. At first Rory thought it meant a divorce. She pushed away any thoughts that were okay with that as she curiously waited.

It wasn't until later that day that she found out Rebecca was pregnant.

…..

As the years passed, Rory finally realized what Jess was to her. He was more than an important person in her life, he was her best friend. He was a father figure to her daughter and he was the one person who never judged her and called her out when she made a mistake.

The day she vowed she wouldn't make the same past mistakes she had before with Jess was for the better. Jess now was a father of two, he had a son and a little girl just born two weeks earlier.

Never once since she had first seen him with Rebecca did he not look happy. After the first kid, he seemed tired but a good tired. Randall was now five years old and he was already so smart. A mini Jess, Liz had called her grandson.

Tori and Randall had become friends too so they saw each other often. It had been hard at first but in time, Rory was able to live with her feelings. The more she saw how Jess was with Rebecca, the more she knew how right they were for each other.

Eventually, Rory realized what Jess was most of all - just as much as he was her best friend, he was the one that got away. But he was also the one who got to be happy and she hoped, that maybe sometime she would get that, too.

 **A/N: the end! I hope it's not terrible. I wasn't sure exactly how to write something that spanned over time and also I wasn't sure how to end it. If it's terrible, don't tell me because I'm not sure I can take it lol But I really hope it's okay and remember you were warned it's not an endgame fic. I feel like this is realistically what should happen. No one has to agree with me, I even have moments where I don't agree with my own opinion on it. I just hope I did justice and didn't do horrible at skipping forward.**


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